CN109553536B - Synthetic method of fatty alkyl dimethyl benzyl quaternary ammonium salt - Google Patents
Synthetic method of fatty alkyl dimethyl benzyl quaternary ammonium salt Download PDFInfo
- Publication number
- CN109553536B CN109553536B CN201710891215.0A CN201710891215A CN109553536B CN 109553536 B CN109553536 B CN 109553536B CN 201710891215 A CN201710891215 A CN 201710891215A CN 109553536 B CN109553536 B CN 109553536B
- Authority
- CN
- China
- Prior art keywords
- alkyl dimethyl
- fatty alkyl
- tertiary amine
- reaction
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of fatty alkyl dimethyl benzyl quaternary ammonium salt. The preparation method of the fatty alkyl dimethyl benzyl quaternary ammonium salt comprises the following steps of carrying out salt forming reaction on fatty alkyl dimethyl tertiary amine and benzyl halide in an organic solvent at the temperature of 30-70 ℃; wherein in the fatty alkyl tertiary amine, R is C6H13～C22H45(ii) a In the benzyl halide, the halogen is chlorine, bromine or iodine; the organic solvent is one or more of methanol, ethanol, n-propanol, isopropanol, acetone and acetonitrile. The preparation method has high yield which can reach more than 90 percent; high purity (up to more than 99%), low water content, good appearance and form of the product, simple post-treatment, low energy consumption, and suitability for industrial production.
Description
Technical Field
The invention relates to a synthetic method of fatty alkyl dimethyl benzyl quaternary ammonium salt.
Background
The fatty alkyl dimethyl benzyl quaternary ammonium salt is a cationic surfactant, belongs to a non-oxidative bactericide, and has very high-efficiency bactericidal capacity. The current methods for synthesizing fatty alkyl dimethyl benzyl quaternary ammonium salt can be divided into two methods. One is synthesized by fatty alkyl dimethyl tertiary amine and benzyl halide; the other is synthesized by halogenated aliphatic alkane and N, N-dimethylbenzylamine.
Document 1(CN 1267405C) discloses the synthesis of a mixture of dodecylbenzylammonium chloride and tetradecylbenzylammonium chloride from the corresponding tertiary amine mixture with benzyl chloride. It should be noted that there are many disadvantages to this approach. Firstly, in order to obtain the alkyl dimethyl benzyl quaternary ammonium salt with higher purity, the method selects benzyl chloride purified by high-temperature atmospheric distillation as a reactant, which undoubtedly increases the energy consumption of the reaction and increases the cost of the reaction. The content of the highly toxic substance benzyl chloride in the final product reaches 4.82 percent at most.
Document 2(US 5414124) reports the synthesis of alkyldimethylbenzyl quaternary ammonium salt solutions in a mixed solvent of glycol and water. The disadvantage of this process is the excessively high reaction temperature and the low concentration of quaternary ammonium salts in the final reactants.
Document 3(RU 2123491) reports that a fatty alkyl dimethyl benzyl quaternary ammonium salt solution with a concentration of 50-80% is finally obtained by reacting a mixed tertiary amine (mainly a fatty alkyl dimethyl tertiary amine with a carbon chain length of 12-16) with benzyl chloride in a mixed solvent of an alkyl diol and water. However, the final product of this method is not highly pure and is a mixture, and it is difficult to separate the purified products of the respective components. In the post-treatment, a higher temperature is required to remove the solvent, which results in poor color, yellow color and incomplete reaction of benzyl chloride.
Although document 4(CN 102807494a) provides a method for synthesizing fatty alkyl dimethyl benzyl ammonium chloride. However, the anhydrous substance prepared by the method has poor purity and is very easy to absorb moisture. Furthermore, the procedure of example 1 disclosed in this method was followed, wherein the molar ratio of dodecyldimethyl tertiary amine to benzyl chloride was 1:0.95, i.e., the dodecyldimethyl tertiary amine was charged in excess, but no specific purification step was disclosed in the method disclosed in CN 102807494A. And 174.4kg of product was obtained, with an impurity content of about 2.09kg (174.4kg x 1.2%) calculated as 98.8% purity of the final product; however, the excess of tertiary amine in the charge was 5.11kg (24mol), much greater than 2.09 kg. In addition, according to the analysis of the disclosed reaction and post-treatment processes, the system has no material loss, but the yield is only 90.3%, and the purity is more than 98%, so that the purification process of the anhydrous substance is not disclosed. If the unreacted raw materials are not purified, the final purity of the product is low, the product is extremely easy to absorb moisture, and the product produced by the method cannot meet the medicinal requirement. Due to the fact that the purity is not high enough, a certain amount of water is added in the subsequent treatment process to improve the stability of the product, the water content of the product is increased, the net purity of the product is reduced, the viscosity of the product is high, slicing and crushing are carried out by a slicing machine, and the product is not easy to process.
Document 5(CN 101525295) also discloses a method for synthesizing fatty alkyl dimethyl benzyl ammonium chloride using urea as a solvent. However, the method has high reaction temperature (130 ℃), and the final product has low content of quaternary ammonium salt and also contains untreated solvent urea, so the method is not suitable for large-scale production.
In document 6(journal of applied biomedicine 12(2014) 245-253), a method for preparing fatty alkyl dimethyl benzyl quaternary ammonium salt by crystallization using butanone as a solvent is given. However, in this process, the final work-up required crystallization at-30 ℃ for 12 h. Such relatively severe conditions are not industrially desirable. Moreover, the final product carries water of crystallization, which, like in document 4, leads to an increase in the water content of the product and a decrease in its net purity.
In document 7(j.phys.chem.,1990,94(1),381-387), a method of synthesis using ethanol as a solvent and crystallization using ethyl acetate, ethyl acetate + ethanol or diethyl ether is given. However, this method requires 3 to 4 crystallizations. This increases the number of production steps, which is not preferable in actual production.
Methods for synthesizing fatty Alkyl dimethylbenzyl quaternary ammonium Salts from halogenated fatty alkanes and N, N-dimethylbenzylamine are also reported in the literature (Kamil Kuca et al, preparation of Benzalkonium Salts differentiation in the Length of a Side Alkyl Chain; Molecules 2007,12, 2341-2347;
et al.A gen(ii) emulsion methods for the quaternization of N, N-dimethyl benzamines with long chain N-alkylbromides; j.appl.biomed.2004,2, 195-198). However, this method is only suitable for the preparation of fatty alkyldimethylbenzyl bromides. The method has low yield of the fatty alkyl dimethyl benzyl chloride synthesized by the method because the chlorinated fatty alkane has weaker activity than the brominated fatty alkane, so the process of forming the quaternary ammonium salt is difficult.
By combining the analysis of the prior art, most of the existing methods for synthesizing the fatty alkyl dimethyl benzyl quaternary ammonium salt are to react a tertiary amine mixture with benzyl chloride, but the purity of the general final product is not high, and the final product contains a large amount of unreacted raw materials and related substances such as benzyl alcohol, benzaldehyde and the like, and can reach the standard of medicinal grade by further refining. And the prepared fatty alkyl dimethyl benzyl quaternary ammonium salt is mostly yellow colloidal or blocky substance, and is very inconvenient to use in subsequent weighing.
Therefore, it is necessary to develop a preparation method for preparing the fatty alkyl dimethyl benzyl quaternary ammonium salt, which has the advantages of high purity, less related substances, less water content, good appearance and shape of the product and easy processing.
Disclosure of Invention
The invention aims to solve the technical problem of overcoming the defects of low yield, toxic by-products, low purity, high water content, unstable aftertreatment, easy color change and the like of the preparation method of the fatty alkyl dimethyl benzyl quaternary ammonium salt in the prior art. The preparation method has the advantages of high yield, high purity, low water content and low reaction temperature, can realize the effects of good appearance and shape of the product and simple post-treatment, can reduce energy consumption, and is suitable for industrial production.
The invention provides a preparation method of fatty alkyl dimethyl benzyl quaternary ammonium salt, which comprises the following steps of carrying out salt forming reaction on fatty alkyl dimethyl tertiary amine and benzyl halide in an organic solvent at the temperature of 30-70 ℃;
wherein in the fatty alkyl dimethyl tertiary amine, R is C6～C22Alkyl groups of (a);
in the benzyl halide, the halogen is chlorine, bromine or iodine;
the organic solvent is one or more of methanol, ethanol, n-propanol, isopropanol, acetone and acetonitrile.
In the fatty alkyl dimethyl tertiary amine, R is preferably C6～C22Even alkyl of (2), more preferably C12H25、C14H29Or C16H33Linear alkyl group of (1).
The molar ratio of the aliphatic alkyl dimethyl tertiary amine to the benzyl halide can be a conventional molar ratio in the salt-forming reaction in the field, and the molar ratio of the aliphatic alkyl dimethyl tertiary amine to the benzyl halide in the invention is preferably 1 (0.9-1.1), more preferably 1: 1.
The dosage of the organic solvent can be the dosage which is conventional in the salt-forming reaction in the field, and the mass ratio of the organic solvent to the fatty alkyl dimethyl tertiary amine is preferably (2-5): 1, more preferably (3-4): 1.
The salt-forming reaction is preferably carried out under anhydrous conditions which are conventional in the art, e.g., without affecting the reaction.
The temperature of the salt forming reaction is preferably 40 to 60 ℃, and more preferably 50 ℃.
The salt-forming reaction is preferably carried out under an inert atmosphere; the inert atmosphere is preferably one or more of nitrogen, argon and helium.
In the salt-forming reaction, the progress of the reaction can be monitored by a monitoring method (e.g., TLC, HPLC, or NMR) which is conventional in the art, and a point at which the benzyl halide compound disappears or is no longer reacted is generally used as a reaction end point. In the invention, the time of the salt forming reaction is preferably 3-5 h.
The salt-forming reaction can also comprise the following post-treatment steps: after the reaction is finished, cooling to separate out a solid; preferably, after the reaction is finished, the reaction system is cooled to-10 ℃ to 10 ℃, crystallized and filtered.
On the basis of the common knowledge in the field, the above preferred conditions can be combined randomly to obtain the preferred embodiments of the invention.
The reagents and starting materials used in the present invention are commercially available.
The positive progress effects of the invention are as follows: the preparation method has high yield which can reach more than 90 percent; high purity (up to more than 99%), low water content, good appearance and form of the product, simple post-treatment, low energy consumption, and suitability for industrial production.
Drawings
FIG. 1 is an HPLC chart of dodecyl dimethyl benzyl ammonium chloride
FIG. 2 shows dodecyl dimethyl benzyl ammonium chloride1H NMR chart
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
EXAMPLE 1 preparation of Hexanyldimethylbenzylammonium bromide
A50L reactor was charged with 4.00kg (31.0mol) of hexyldimethyltertiary amine, 5.83kg (34.1mol) of benzyl bromide and 20.00kg of isopropanol and stirred at 70 ℃ for 3 hours. Then the temperature is reduced to-10 ℃. After the solid precipitated, it was filtered and dried to obtain 8.61kg of white solid with a total yield of 92.6%. The purity of the hexyl dimethyl benzyl ammonium bromide is 99.4 percent.
EXAMPLE 2 preparation of octyl dimethyl benzyl ammonium chloride
A50L reactor was charged with 4.50kg (28.7mol) of octyl dimethyl tertiary amine, 3.81kg (30.1mol) of benzyl chloride and 18.00kg of acetonitrile, and stirred at 50 ℃ for 5 hours. Then the temperature is reduced to 10 ℃. After the solid precipitated, it was filtered and dried to obtain 7.48kg of white solid with a total yield of 91.9%. The purity of the octyl dimethyl benzyl ammonium chloride is 99.5 percent.
EXAMPLE 3 preparation of decyl dimethyl benzyl ammonium iodide
A50L reactor was charged with 4.00kg (21.6mol) of decyl dimethyl tertiary amine, 4.48kg (20.5mol) of benzyl iodide and 12.00kg of methanol, and stirred at 60 ℃ for 3 hours. Then the temperature is reduced to-10 ℃. After the solid precipitated, it was filtered and dried to obtain 7.70kg of white solid with a total yield of 93.2%. The purity of the decyl dimethyl benzyl ammonium iodide is 99.3%.
EXAMPLE 4 preparation of dodecyl dimethyl benzyl ammonium chloride
100.00kg (469.5mol) of dodecyldimethyl tertiary amine, 62.40kg (493.0mol) of benzyl chloride and 300.00kg of acetone are charged into a 1000L reaction kettle and stirred at 40 ℃ for 3 h. Then the temperature is reduced to 0 ℃. After the solid precipitated, it was filtered and dried to obtain 145.88kg of a white solid with a total yield of 92.5%. The purity of the dodecyl dimethyl benzyl ammonium chloride is 99.6 percent.
EXAMPLE 5 preparation of dodecyl dimethyl benzyl ammonium chloride
100.00kg (469.5mol) of dodecyldimethyl tertiary amine, 59.42kg (469.5mol) of benzyl chloride and 400.00kg of isopropanol are charged in a 1000L reactor and stirred at 30 ℃ for 5 h. Then the temperature is reduced to 5 ℃. After the solid precipitated, it was filtered and dried to obtain 147.30kg of a white solid with a total yield of 92.4%. The purity of the dodecyl dimethyl benzyl ammonium chloride is 99.7 percent.
EXAMPLE 6 preparation of tetradecyldimethylbenzylammonium chloride
75.00kg (311.2mol) of tetradecyldimethylamine tertiary amine, 35.45kg (280.1mol) of benzyl chloride and 250.00kg of ethanol were charged in a 500L reactor, and stirred at 40 ℃ for 5 hours. Then the temperature is reduced to-5 ℃. After the solid is precipitated, the solid is filtered and dried to obtain 94.00kg of white solid, and the total yield is 91.3%. The purity of tetradecyl dimethyl benzyl ammonium chloride is 99.6%.
Example 7 preparation of tetradecyldimethylbenzylammonium chloride
75.00kg (311.2mol) of tetradecyldimethylamine tertiary amine, 37.40kg (295.6mol) of benzyl chloride and 200.00kg of acetonitrile were charged in a 500L reactor and stirred at 50 ℃ for 3 hours. Then the temperature is reduced to 0 ℃. After the solid is precipitated, the solution is filtered and dried to obtain 98.31kg of white solid with the total yield of 90.5 percent. The purity of tetradecyl dimethyl benzyl ammonium chloride is 99.5%.
EXAMPLE 8 preparation of hexadecyldimethylbenzyl ammonium chloride
A50L reactor was charged with 7.00kg (26.0mol) of cetyldimethyl tertiary amine, 3.36kg (26.5mol) of benzyl chloride and 17.50kg of n-propanol and stirred at 50 ℃ for 3 h. Then the temperature is reduced to-5 ℃. After the solid precipitated, it was filtered and dried to give 9.47kg of a white solid with a total yield of 92.1%. The purity of the hexadecyl dimethyl benzyl ammonium chloride is 99.5 percent.
EXAMPLE 9 preparation of hexadecyldimethylbenzyl ammonium chloride
A50L reactor was charged with 7.00kg (26.0mol) of hexadecyldimethyl tertiary amine, 3.22kg (25.5mol) of benzyl chloride and 25.00kg of methanol, and stirred at 30 ℃ for 4 hours. Then the temperature is reduced to-5 ℃. After the solid is precipitated, the solution is filtered and dried to obtain 9.16kg of white solid with the total yield of 90.9 percent. The purity of the hexadecyl dimethyl benzyl ammonium chloride is 99.6 percent.
EXAMPLE 10 preparation of octadecyl dimethyl benzyl ammonium Bromide
A50L reactor was charged with 8.00kg (26.9mol) of octadecyl dimethyl tertiary amine, 4.38kg (25.6mol) of benzyl bromide and 16.00kg of acetonitrile, and stirred at 60 ℃ for 3 h. Then the temperature is reduced to 10 ℃. After the solid precipitated, it was filtered and dried to obtain 11.14kg of a white solid with a total yield of 93.0%. The purity of octadecyl dimethyl benzyl ammonium bromide is 99.4%.
EXAMPLE 11 preparation of eicosyldimethylbenzylammonium iodide
A50L reactor was charged with 4.00kg (12.3mol) of eicosyldimethylamine tertiary amine, 2.76kg (12.7mol) of benzyl iodide and 20.00kg of acetone, and stirred at 40 ℃ for 3 hours. Then the temperature is reduced to 5 ℃. After the solid precipitated, it was filtered and dried to obtain 6.18kg of white solid with a total yield of 92.5%. The purity of eicosyldimethylbenzylammonium iodide was 99.6%.
EXAMPLE 12 preparation of behenyldimethylbenzylammonium chloride
A50L reactor was charged with 6.00kg (17.0mol) of behenyldimethyl tertiary amine, 2.10kg (16.7mol) of benzyl chloride and 21.00kg of ethanol, and stirred at 50 ℃ for 4 h. Then the temperature is reduced to 0 ℃. After the solid precipitated, it was filtered and dried to obtain 7.27kg of white solid with a total yield of 90.8%. The purity of the behenyl dimethyl benzyl ammonium chloride was 99.5%.
Comparative example 1
A comparison of the results was made according to the disclosure in example 1 of CN 102807494 a.
Comparative example 2
The preparation of dodecyldimethylbenzylammonium chloride was carried out according to the method described in the literature "Journal of applied biomedicine 12(2014) 245-253" for comparison. The method comprises the following specific steps: a250 mL flask was charged with 21.3g (0.1mol) of dodecyldimethyl tertiary amine, 12.6g (0.1mol) of benzyl chloride and 100mL of butanone, and heated to 80 ℃ for reflux reaction for 12 hours. Then 1.8mL of water was added and the reaction was continued at reflux for 6 h. Then cooling to-30 ℃ and cooling for crystallization for 12 h. The crude product was filtered and dried under reduced pressure to give 32.5g of dodecyldimethylbenzylammonium chloride containing two molecules of crystal water, with a yield of 96.0%, a purity of 95.3% and a moisture of 9.6%.
Comparative example 3
The preparation of dodecyldimethylbenzylammonium chloride was carried out according to the method described in the "Journal of applied biomedicine 12(2014) 245-253" in contrast to comparative example 2, except that no water was added during the working-up. The method comprises the following specific steps: a250 mL flask was charged with 21.3g (0.1mol) of dodecyldimethyl tertiary amine, 12.6g (0.1mol) of benzyl chloride, and 100mL of butanone, and heated to 80 ℃ for reflux reaction for 18 hours. Then cooling to-30 ℃ and cooling for crystallization for 12 h. The crude product was filtered and dried under reduced pressure to give 32.7g of dodecyldimethylbenzylammonium chloride without water of crystallization in 90.4% yield, 94.1% purity and 0.8% moisture.
Comparative example 4
The preparation of dodecyldimethylbenzylammonium chloride was carried out according to the method of the document "j.phys.chem., 1990,94(1), 381-387", for comparison. The method comprises the following specific steps: a250 mL flask was charged with 21.3g (0.1mol) of dodecyldimethyl tertiary amine, 12.6g (0.1mol) of benzyl chloride and 100mL of absolute ethanol, and heated to 80 ℃ for reflux reaction for 36-48 h. After the reaction, the solvent and unreacted materials were evaporated. The crude product was crystallized 3 times from ethyl acetate. Drying under reduced pressure gave 21.80g of dodecyldimethylbenzylammonium chloride as a solid. The yield was 64.3%, the purity was 99.3%, and the water content was 0.9%.
Comparative example 5
The preparation of dodecyldimethylbenzylammonium chloride was carried out according to the methods described in the references "Molecules 2007,12, 2341-2347" and "j.appl.biomed.2004, 2, 195-198" for comparison. The method comprises the following specific steps: a50 mL flask was charged with 1.0g (0.007mol) of dimethylbenzylamine, 2.0g (0.01mol) of chlorododecane, and 25mL of absolute ethanol, and heated to 80 ℃ for 28 hours under reflux. After the reaction was completed, the solvent was evaporated to dryness. The crude product was subjected to column chromatography with chloroform/methanol (100/1) eluent. Finally, decompression drying is carried out to obtain 0.84g of dodecyl dimethyl benzyl ammonium chloride solid. The yield was 35.3%, the purity was 99.2%, and the water content was 0.9%.
Effect example 1
The moisture and purity of examples 1 to 12 and comparative examples 1 to 5 were examined, and the results are shown in Table 1.
TABLE 1 comparison of results for examples 1-6 and comparative examples 1-4
In table 1, the purity data is calculated by the mass of the dried fatty alkyl dimethyl benzyl quaternary ammonium salt, and is independent of the water content. As can be seen from the experimental data in Table 1, the yield of the fatty alkyl dimethyl benzyl quaternary ammonium salt produced by the method can reach more than 90%, the water content is less than 1.0%, and the purity can reach more than 99%.
In the process disclosed in CN 102807494a, no specific purification step is disclosed. The water content of the product was 10.7% calculated on the basis of 174.4kg of product obtained and 18.6kg of water added.
Comparative example 2, although the yield was 96% higher than the present invention, the purity was 95.3% much lower than the present invention; comparative example 3, crystallization was carried out without adding water on the basis of comparative example 2, and the total yield was 90.4% close to the present invention, and the purity was 94.1% much lower than the present invention. However, the specific procedure of comparative example 3 is carried out for a longer reaction time and at a higher reaction temperature than the present invention. It is presumed that too high a reaction temperature or too long a reaction time leads to partial decomposition of the raw materials, so that the final product of comparative example 3 has a purity far lower than that of the present invention. Most importantly, the crystallization temperature in comparative examples 2 and 3 needs to be-30 ℃, liquid ammonia is used for cooling in industrial production, and only brine ice is used for cooling at-10 ℃ to 10 ℃ in the invention. Compared with the former, the cost of the former is 5-10 times of that of the latter.
Comparative examples 4 and 5, both of which yield was lower than the present invention due to the crystallization method and the change of the solvent or starting material.
Claims (10)
1. A preparation method of fatty alkyl dimethyl benzyl quaternary ammonium salt is characterized by comprising the following steps of carrying out salt forming reaction on fatty alkyl dimethyl tertiary amine and benzyl halide in an organic solvent at 30-70 ℃;
wherein in the fatty alkyl dimethyl tertiary amine, R is C6～C22Alkyl groups of (a);
in the benzyl halide, the halogen is chlorine, bromine or iodine;
the organic solvent is one or more of methanol, ethanol, n-propanol, isopropanol, acetone and acetonitrile;
the mass ratio of the organic solvent to the fatty alkyl dimethyl tertiary amine is (2-5) to 1; the molar ratio of the fatty alkyl dimethyl tertiary amine to the benzyl halide is 1 (0.9-1.1); the salt-forming reaction is carried out in an inert atmosphere;
the time of the salt forming reaction is 3-5 h;
the salt-forming reaction also comprises the following post-treatment steps: after the reaction is finished, cooling the reaction system to-10 ℃, crystallizing and filtering.
2. The method according to claim 1, wherein R in said aliphatic alkyl dimethyl tertiary amine is C6～C22An even alkyl group.
3. The method of claim 1, wherein R is C12H25、C14H29Or C16H33Linear alkyl group of (1).
4. The method according to claim 1, wherein the reaction mixture,
the molar ratio of the fatty alkyl dimethyl tertiary amine to the benzyl halide is 1: 1.
5. The method according to claim 1, wherein the reaction mixture,
the mass ratio of the organic solvent to the fatty alkyl dimethyl tertiary amine is (3-4) to 1.
6. The process according to any one of claims 1 to 5, wherein the salt-forming reaction is carried out under anhydrous conditions.
7. The production method according to any one of claims 1 to 5,
the reaction temperature is 40-60 ℃.
8. The method of claim 7, wherein the reaction temperature is 50 ℃.
9. The method according to claim 1, wherein the reaction mixture,
the inert atmosphere is one or more of nitrogen, argon and helium.
10. The process according to claim 1, wherein the reaction system is cooled to-5 ℃ to 5 ℃ after the reaction is completed, crystallized, filtered and dried.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710891215.0A CN109553536B (en) | 2017-09-27 | 2017-09-27 | Synthetic method of fatty alkyl dimethyl benzyl quaternary ammonium salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710891215.0A CN109553536B (en) | 2017-09-27 | 2017-09-27 | Synthetic method of fatty alkyl dimethyl benzyl quaternary ammonium salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109553536A CN109553536A (en) | 2019-04-02 |
| CN109553536B true CN109553536B (en) | 2022-05-03 |
Family
ID=65864137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710891215.0A Active CN109553536B (en) | 2017-09-27 | 2017-09-27 | Synthetic method of fatty alkyl dimethyl benzyl quaternary ammonium salt |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109553536B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527106B (en) * | 2020-04-16 | 2023-10-20 | 广东先强药业有限公司 | Preparation method of pharmaceutical grade sitagliptin chloride |
| CN115124428A (en) * | 2022-07-20 | 2022-09-30 | 山东鑫泰水处理技术股份有限公司 | Composite bactericide containing dialkyl methyl benzyl quaternary ammonium salt and preparation method thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5414124A (en) * | 1993-01-19 | 1995-05-09 | Huntington Laboratories, Inc. | Method of preparing quarternary ammonium formulations with high flash points |
| CN103351301A (en) * | 2013-07-01 | 2013-10-16 | 安徽奔马先端科技有限公司 | Synthetic method for high-purity quaternary ammonium salt |
| WO2013162924A1 (en) * | 2012-04-24 | 2013-10-31 | Stepan Company | Synergistic surfactant blends |
| CN104031243A (en) * | 2014-06-24 | 2014-09-10 | 上海大学 | Quaternary ammonium salt epoxy resin curing accelerator and preparation method thereof |
| CN104163763A (en) * | 2014-07-14 | 2014-11-26 | 安徽奔马先端科技有限公司 | New synthesis method of high purity quaternary ammonium salt |
| CN106946716A (en) * | 2017-03-24 | 2017-07-14 | 吴琏 | A kind of benzalkonium chloride monomer synthesis technique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103896781A (en) * | 2014-03-25 | 2014-07-02 | 徐州工业职业技术学院 | Preparation method of benzyltriethylammonium chloride |
-
2017
- 2017-09-27 CN CN201710891215.0A patent/CN109553536B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5414124A (en) * | 1993-01-19 | 1995-05-09 | Huntington Laboratories, Inc. | Method of preparing quarternary ammonium formulations with high flash points |
| WO2013162924A1 (en) * | 2012-04-24 | 2013-10-31 | Stepan Company | Synergistic surfactant blends |
| CN103351301A (en) * | 2013-07-01 | 2013-10-16 | 安徽奔马先端科技有限公司 | Synthetic method for high-purity quaternary ammonium salt |
| CN104031243A (en) * | 2014-06-24 | 2014-09-10 | 上海大学 | Quaternary ammonium salt epoxy resin curing accelerator and preparation method thereof |
| CN104163763A (en) * | 2014-07-14 | 2014-11-26 | 安徽奔马先端科技有限公司 | New synthesis method of high purity quaternary ammonium salt |
| CN106946716A (en) * | 2017-03-24 | 2017-07-14 | 吴琏 | A kind of benzalkonium chloride monomer synthesis technique |
Non-Patent Citations (3)
| Title |
|---|
| Physicochemical characterization of bromide mono- and dimeric surfactants with phenyl and cyclohexyl rings in the head group;Victoria Isabel Martin等;《Journal of Colloid and Interface Science》;20110626;第363卷;第284-294页 * |
| Ternary Water in Oil Microemulsions Made of Cationic Surfactants, Water, and Aromatic Solvents. 1. Water Solubility Studies;A. Jada等;《J. Phys. Chem.》;19901231;第94卷(第1期);第381-387页 * |
| Victoria Isabel Martin等.Physicochemical characterization of bromide mono- and dimeric surfactants with phenyl and cyclohexyl rings in the head group.《Journal of Colloid and Interface Science》.2011,第363卷第284-294页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109553536A (en) | 2019-04-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR101115412B1 (en) | New preparation of hydroxychloroquine | |
| EP2640714A1 (en) | Process for the preparation of 2-oxo-[1,3]dioxolane-4-carboxylic acid esters | |
| CN109553536B (en) | Synthetic method of fatty alkyl dimethyl benzyl quaternary ammonium salt | |
| CN100522920C (en) | Method for preparing 4-bromine 2,6-difluoro benzoic acid | |
| CN109553539B (en) | Preparation method of benzalkonium chloride | |
| CN106699595B (en) | A kind of scheme for lacosamide preparation method | |
| CN102548959B (en) | Production method for an alkyl isocyanate | |
| CN112479938B (en) | Preparation method of N-cyclohexyl-2-aminoethanesulfonic acid | |
| EP0127128B1 (en) | Process for the conversion of the e isomer of 1,2-diphenyl-1-(4-(2-dimethylaminoethoxy)-phenyl)-1-butene to tamoxifen hcl | |
| CN107673984B (en) | Preparation method of levetiracetam key intermediate (S) -2-aminobutanamide salt | |
| KR100401284B1 (en) | Method for preparing 1-bromoethyl acetate | |
| US20120123136A1 (en) | Process for the preparation of 2-oxo-[1,3] dioxolane-4-carboxylic acid esters | |
| KR100203457B1 (en) | Process for terbinafine | |
| CN114853619B (en) | Preparation method of N-methyltyramine hydrochloride suitable for industrial production | |
| JP3867309B2 (en) | (E) Method for producing -2 ', 4'-dichloroacetophenone oxime | |
| CN113735693B (en) | Synthesis method of resveratrol dimethyl ether | |
| IL45098A (en) | Process for preparing triacetonamine | |
| CN110156697B (en) | Synthetic method of 1,2-dimethyl-1,4,5,6-tetrahydropyrimidine | |
| JP7394995B2 (en) | Method for producing a new crystalline form of 1-(4-benzyloxy-benzyl)-3-methyl-thiourea | |
| CN112209838B (en) | Preparation method of butenaphthol hydrochloride | |
| US5994553A (en) | Method for preparing 2-mercaptothiazole | |
| KR100543345B1 (en) | A manufacturing process for 6-chlorobenzoxazol-2-one | |
| CN111057001A (en) | Preparation method of quinolone malonate compound | |
| CN117777052A (en) | Preparation method of phenothiazine | |
| CN111116460A (en) | Synthesis method of 2-chloro-4-hydroxypyridine-3-formaldehyde hydrobromide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |